Treatment of cellulose textiles



rials so as to achieveimproved crease resistance and 3,165,424 TREATMENT on CELLULOSE TEXTILES .iosaf Ktinig, Siegburg, Rhineland, and Egon N. Petersen,

Neumunster, Germany, assignors to Phrix-Werke Aktiengesellschaft, Hamburg, Germany No Drawing. Filed Apr. 6, 1960, Ser.

Claims priority, applicatzignsgsermany, Apr. 6, H59,

11 Ciaims. cl. 117-1s9.4

The present invention relates to the treatment of textile materials so as to render the same crease resistant and wrinkle resistant, and more particularly to the treatment of cellulose materials to impart crease resistant and wrinkle resistant properties to the same while maintaining the strength of the material.

' It is known to treat textile materials, such as threads, fibers, yarns and webs made of material or regenerated cellulose, 'with acidic mixtures of water-soluble sub stances which can be transformed under action of heat into an insoluble resin-like state, in order to render the textile materials crease-proof or to stabilize the textile materials against shrinkage during washing. It is known to impregnate textile materials of the above described type with solutions of aldehydes such as formaldehyde or glyoxal which contain acidic catalysts, or pro-condeni sates of urea-formaldehyde or melamine-formaldehyde,

these solutions being condensed on the material to become insoluble under the action of heat. Such products tend to render the textile material still and brittle and/ or to impair the strength characteristics of the textile material.

According to a different finishing method, the textile material is coated with cellulose ethers of different kinds.

If such 'eth'ers possess a low degree of alkylation sothat they are soluble only in alkalides but not in water, they are undesirable in the treatment of textile materials made of cellulose because'they require a comparatively high concentration of an alkali. The alkali causes swelling of the material'and thereby prevents rapid penetration of the cellulose ether. Cellulose others with a higher degree of alkylation possess the advantage that they are soluble in water. However, when using such cellulose ethers,the problem arises that they must be made waterinsoluble in order to insure that the textile materials treated with such ethers remain washproof.

It is also known to utilize solely alkali-soluble, i.e., water-insoluble cellulose ethers, such as simple alkyl ethers, carboxyl ethers, mixed alkyl-oxyalkyl ethersor mixed alkyl-carboxyalkyl ethers together with solutions which, upon' heating, produce synthetic resins. prior methods were found impractical in actual use partly because the individual components of such mixtures are often incompatible. so that one obtain turbid, easily floc culable suspensions. alkyl cellulose products, such as methyl cellulose or methyl ethyl cellulose, which preferably should be completely etherified because otherwise they are not sufiiciently water-soluble, are not suitable because they can not prevent the stiffness and brittleness of a textile mate rial caused by the deposition of synthetic resins.

' fixed in a washproof manner. I

It is accordingly a primary object of the present-invention to provide a process of treating cellulose matewrinkle resistance.

It is another object of the present invention to provide a method of treating cellulose materials with a treating Simple as Well as mixed etherified a ss ad Patented Jan. 12, 1965 liquor so that the treated cellulose material has good crease resistance and wrinkle resistance along with high strength characteristics and a good feel.

In general the present invention provides a method of providing crease resistance to cellulose material by a procedure which avoids all of the above and other enumerated disadvantages of the prior art.

Other objects: and advantages of the present invention will be apparent, from a further reading of the specification and of the appended claims.

With the above and other objects in view, the present invention mainly concerns a method of improving the upon heating to a predetermined temperature below the temperature at which damage to the cellulose textile material occurs is transformed into an insoluble resinous substance, the water soluble resin-forming substance con taining hydroxyl. groups, and also containing in solution a water soluble alkyloxy cellulose containing free bydroxyl'groups, and heating the thus treated cellulose textile material to the predetermined temperature so as to convert the water soluble resin-forming substance into an insoluble resinous substance and to cause cross linking reaction between the' same and the water soluble alkyloxy cellulose, thereby forming a treated cellulose textile material having improved properties.

The treating of the textile material may be carried out by spraying the same with the aqueous liquor, but is preferably accomplished by immersing thetextile material in the liquor. The heating temperature is generally above 100 C. and is most-preferably at a temperature between 100 and 150 C.

The method of the present invention makes it possible to improve textile material of the cellulose type with respect to the crease resistance thereof while retaining the properties of strength and also while giving to the textile material a good feel. The method of the present invention is particularly advantageous in that the crease resistance which is imparted to the textiles remains even after laundering. This is achieved in accordance with the present inventionby the use of the cellulose mixed ether, that is the alkoxy cellulose which contains free hydroxyl groups in the cellulose molecule, these free hydroxyl Such" groups reacting with and cross linking the resin-forming substance, for example the dimethylol urea. The cellulose mixed ether also has the advantage'of a good water solubility and the possibility of producing stable, non-flocculating solutions.

The alkyloxy alkyl celluloses which are utilized'in the present invention are produced by reacting an alkali cellulose with about 1 mol of a common alkylating agent and'about 3 mols of a common alkoxyl-ating agent, calculated per each mol of glucose anhydride of the cellulose.

I alkoxylating agent it is possible to use a lower alkylene Particularly good properties of the treated textile with re spect to crease or wrinkle resistance and good feel are achieved by maintaining the mol ratios of the produced cellulose ether as set forth above.

Celluloses of this type are suitable as starting material for the production of the mixed cellulose ethers of the present invention. As alkylating agent it is possible to use a "lowe'r alkyl halogenide such as methyl bromide,

methyl chloride, ethyl bromide and ethyl chloride AS glyoxal (the glyoxal preferably being used together With an aldehyde carboxylic acid such as glyoxylic'acid as 'condensation catalyst), urea-formaldehyde pre-condensa't es forth liquors under the same conditions gave the results =set forthin Table 2. I

, oxide such as ethylene oxide, propylene oxide, ethylene I magnesium chloride, aluminum chloride, ammonium chlo-f ride,-ammonium nitrate, borax, etc. 1

Among the suitable resin-forming substances for the purpose of the present invention are formaldehyde or such as methylol urea, dimethylol urea, melamine-formal-v dehyde condensates, methylol biuret, dimethylol biuret, the reaction product in neutral to slightly alkaline medium of methylol urea and glyoxal and similar products;

The textile material which has been treated with the liquor in accordance with the present invention, which actually have been impregnated with the liquor, for example'by spraying the liquor onto the textile material or preferably by immersing the material in the liquor, is

treated to remove the excess of liquor'for exampleby pressing or by centrifuging the material and this predried textile material can be heated to a temperature up to 150 C. depending upon the duration of heating. 7 The Y drying and heating can also be carried out in a single step.

The following examples, are given to illustrate the ,Tqble 2 Oreaseanglein Crease angle in degreesdry degreeswet V Cellulose mixedether,molratio of celluloserethyl after After Feel cliloridezalkylene Before filaun- Before launoxide launderiugs launderings dering m boilderiug 1n boilingwater i ingwater 115/110 1 113/110 124/127 135/137 Veryd a V 00 104/102 .109/101 109/101 140/145 Insuificient.- 104/107 110/107 es/100 115/110 D0. UntreatedmaterieL. 109 107 100 e 116/130 125 120 -Liiup.

Further comparative tests were carried outusing; liquors '(a) without cellulosederivative, (b) with ZgLper liter of carboxy methyl cellulose instead ofthecellulose mixed ether, (0) with the 2 g.: per. liter'ofthe cellulose mixed ether, that is the ethyloxyethyl"celluloselof the mol ratio 1:1 :3, and acellu'lose poplin was treated with the Y diiferentf liquors; The results were compared and also 10 g. of magnesium chloride as catalyst and 2 g. of ethyl- 1 oxyethyl cellulose (the mol ratio of the, components used to form the cellulose, calculated on the glucose anhydride, of cellulose to ethyl chloride to ethylene oxide with 7 compared with (0.) untreated material, these'results being set forth in Table 3.below.'

Tab/63 r w Crease Angle in Shearing Liquor 7 before degrees" strength; Feel .'launderafter boil turns ingwash Without cellulose derivative. 140 141 "124 126 580 Limp. 2g/1.earboxyrnethyleellulose. 128/130 5118/107 623' Do. 2 g./ l. cellulose mixed ether 7 148/150 {139/134 780 Very molratio,1:1:3. v 1 good." Untreated material. 84/88 1,057 Limp. V,

:For the productionofthe cellulose mixedether with the mol ratio of cellulose to ethylchloride ,to ethylene oxide of 1:1:3' (calculating the cellulose as glucose 1: 1:3 The bath temperature is 35-40 C., the pH value of the treatment solution is 3.5. Thesteeped materialis pressed, dried and heated to a temperature of;145 C. for

7 minutes.

For comparison purposes,samples of the same cotton fabric were treated under the same conditions withliquors which instead of containing the etherified cellulose ethyloxyethyl cellulose in a mol ratio of 1:113, contained ethyloxy cellulose which was produced in a ratio of 0121- 1 luloseicalculated as glucose anhydride) to ethyl chloride to ethylene oxide in a mol ratio of 1:1:2 andin another test in a mol ratio of 1:1;4'. Y The creaseangles'in Weft and warp threads and the feel characteristics of the treated samples and of the untreated samples were determined and are set forth in the following table:- e

v Table 1' Crease angle inv Crease angle in 7 degrees dry degrees-wet Cellulose mixed ether, mol ratio of I eellulosezethyl After ,After Feel ehloridezalkylene Before 5 laun- Before 5 launox'ide launderings launderings dering inboildaring in'boiling wat er ing water I 1: 1:3 129/ 124 118/121 143/131 124/114 Veryd 0o 121:2 86/86 80/79 129/120 110/105 Li i'np. 1:124 V 116/107 95/99 ,144/146 115/116 D0. Untreated material" 101/ 108 91/99 124/121 110/108 Do.

anhydr'ide), pine sulfite :celluloseat a temperature .of

.18 to 20" 0.18 immersedfor 1 hour in' '19 sodium hydroxide, pressed under a pressing factor of ,30a11d" comminuted for an hour-,

free tetrahydrofurane-at a ternperatureof, 80 C for .5 V

The yellowish-brown reaction"productq'is filtered 01f by suction, pressed sharply-and dried under vacuum over calcium chloride. The product is easilysoluble in cold water and no fiber residue remains upon dissolution. The

Y yieldof thevdry reaction product is 60 to .g.

The diluting agent must be peroxide-free, ;To removethe peroxideithe. tetrahydrofurane is allowed to stand with concentrated potassium hydroxide with shaking frorn tirne to time, and after separation of the .potassium hydroxide liquor is'rectified. a v a I I I EXAMPLE .II' V A treating 'liquidis used containing aper"liter l00 grams of technicalglyoxal .(consisting of 20% glyoxalic ,acid, 50% acetic acid and 30% glyorgal),"25 grams of technical borax and 2 grams. of an ethyloxyethyl cellu- .lose (molar relationship 111:3) prepared asndescribed in: Example I The solution 11am pH or 3.7. V

' A rayon shirt material having a crease angleiof 76 in the warp and of 81" in theweft and 'a rub resistance of 1075 passes (at'500gramspreload) isjtreated in the above treating liquid for two minutes,=-thereafter pressed to 9 0% moisture content and thengdried at; 909C; I

Theltreatriient of cellulose poplin with the, above 'set The thus treatedigoods were, found to haveinfwarp and weft, respectively, a. crease angle of 157 /1512 7 after one washing withfsodium-lauryl sulfonate of119/ 0121 and aiub' r'esistancevalueof 779.

A sample of the same material was treated under the same conditions as described above,'with a treating liquid of the above described composition; however omitting the mixed cellulose ether. The dried material showed the following values: a I

Crease angle 145/147, or 110/110 after one washing with sodium lauryl sulfonate; rub resistance: 664 passes (with 500v grams preload).

EXAMPLE III A rayon shirt material as described in Example II is soaked in a treating liquid containing 90 grams of the reaction product obtained by reaction of dirnethylol urea and glyoxal in aqueous solution at a pH of 7.5, 11.5 grams of AlCl .6H O, 10 grams of boric acid and 2 grams of the mixed cellulose ether described in Example II. The pH-of the treating liquid is 3.6. Liquidis squeezed off to a residual moisture content of 100% and the material is then dried at between 100 and 110 C.

The thus treated material has a crease angle of 123/ 115, or of 108/ 120 after one washing'with sodium lauryl sulfonate, a rub resistance of 890 and pleasant'soft feel (touch).

A sample of the same material was finished under identical conditions with the exception that the treating liquid did not contain a mixed cellulose ether. The dried goods had the fol-lowing dry-crease angle:

103/-108, or 93/91 afterione washing with sodium lauryl sulfona te; rub resistance was 856 passes with 500 gram preload. f

' j EXAMPLE IV is then adjusted with concentrated hydrochloric acid to a pH of 5.7 under. the-addition of 8 grams Nl-l NO A sample of the ,rayon shirt material of Example III is then soaked. at a temperature of about 35 in this solution which has a pH of 5.7. The material is then squeezed and dried at 100 C. and thereafter hardened for six minutes at 130 C.

I i The crease angles inl'w arp and weft of the thus finished material are 144-/ 133, or 114/ 119 after one wash? ing with sodium lauryl sulfonate; rub resistance: 670.

The material finished with the same treating liquid except for the absence of'cellulose ether and under otherwise similar conditions has a crease angle of 128/131, or 11 l/111. after one washing with sodiuin laurylsulfonate and a rub resistance of 659.

EXAMPLE v A treating liquid is prepared which contains per liter 100 grams of dimethylol urea 100%, grams of NH NO and 2 grams of the ethyloxyethyl cellulose (molar relationship 1:1:3) similar to the ether used in Example Ill. A sample of the rayon shirtmaterial'of Example 111 is soaked in this treating liquid and after removal of excess liquid by squeezing, the sampleis subjected to'a single drying step carried out forfive minutes at 130 C.

The crease angles in warp and Weft of the treated material are 142/140, or 122/130 after one washing with sodium lauryl sulfonate. Rub resistance: 610. A sample of similar material finished with a treating liquid free of the addition of cellulose ether has crease angles-of '129/129, or 115/127.a'fter one washing with sodium lauryl sulfonate. Rub resistance: 540.

Without further analysis, the foregoing will so fully standpoint of prior art, fairly constitute essential characteristics of the .generic or; specific aspects of this invention and, therefore, such adaptations should and are intended to be comprehended within the meaning and range of equivalence of the following claims.

' What is claimed as new and desired to be securedby taining ether groups and also containing free hydroxyl reveal the gist of the present. invention that others can by applying current knowledge readily'adapt it for .varigroups formed by the reaction of an alkali cellulose with about 1 mol of an alkylating agent and about 3 mols of an alkoxylating agent calculated per each mol of glucose anhydride of said alkali cellulose; and heating the thus treated cellulose textile material to said predetermined temperature so as to convert said water soluble resin-forming substance into an insoluble, resinous sub-: stance and to cause cross linking reaction between the same and said water soluble alkyloxy alkyl. cellulose, thereby forming a treated cellulose textilematerial having improved properties.

2. Method of improving properties such as the crease resistance and non-shrinking properties of cellulose textiles, comprising the steps of treating a cellulosetextile material with an acid aqueous liquor containing in solution a water soluble resin-forming substance which upon heating to a temperature between and C. is transformed into an insoluble resinousvsubstance, said water soluble resin-forming substance containing. hydroxyl groups, and also containing in solution a water soluble alkyloxy alkyl cellulose mixed ether. containing ether groups and also containing free hydroxyl groups formed by the reaction of an alkali cellulose with about lmol of an alkylating agent and about 3 mols of an alkoxylating agent calculated per each molof glucose anhydride of said alkali cellulose; and heating the thustreated cellulose textile material tosaid temperature so as to convert said water soluble resin-forming substance into an insoluble resinous substance and to cause cross linking reaction between the sameand said watersoluble alkyloxy alkyl cellulose, thereby forming a treated cellulosetextile material having improved properties.

'3; Method of improving properties such as the crease resistance and non-shrinking properties of cellulose textiles, comprising the steps of treating acellulose textile material'with an acid aqueous liquor containing in. solution a water soluble resin-forming substance which upon heating to a predeterminedtemperature below the temterial occurs is transformed into an insoluble resinous substance, said Water soluble resin-forming substance containing hydroxyl groups, and also containing in solution a water soluble alkyloxy alkyl cellulose mixed ether containing ether groups and also containing free hydroxyl groups formed by the reaction of an alkali cellulose with about 1 mol ofa lower alkyl halogenide as, an alkylating agent and about 3 mols of a lower alkylene oxide as an alkoxylatingagent calculated per eachmol of glucose anhydride of saidalkali cellulose; and heating the thus treated cellulose textile material to said predetermined temperature so as. to convert said water soluble resin-forming substance into an insoluble resinous substance and to cause cross linking reaction between the same and said, water soluble alkylox'y; alkyl cellulose, thereby forming 21 treated cellulose textile material having improved properties.

4; Method of improving properties such'as the crease resistance and non-shrinking properties of cellulose textiles, comprising the steps ;of treating a cellulose textile 'material'withan acid aqueous liquor containing in solutiona water soluble resin-forming substance whichupon j heating-to a predetermined temperature below the temperature at which damage to said cellulose textile ma-zx terial occurs is transformed into an insoluble resinous,"- substance said water soluble resin-forming substance containing hydroxyl groups, and also containing in solution a Water soluble alkyloxy alkyl cellulose mixed ,ether 7 containing ether groups and also containing free hydroxyl groups formed by the reaction of an alkali cellulose with about 1 mol of an alkylating agent selected from the group consisting of methyl bromide, methyl chloride, ethyl bromide and ethyl chloride'and'about? r mols of an alkoxylating agent selected from the group consisting of ethylene oxide, propylene oxide and ethylene chlorohydrinycalculated ,per each mol of glucose an! hydride of said alkali cellulose; and heatingvithe thus 7 7:.-'Method of. improving properties such asi thecrease resistance and non-shrinkingproperties of cellulose textiles, comprising vthe stepsfof treatinga cellulose textile material with 'anyacid aqueousflliquorfliaving a pHbe ':tween 3 and 5 and containing in solution a water soluble resin-forming substance which upon'heatingato atemperature between '100 and 150" C. is "transformed into an insoluble resinous substance,: said water soluble resin- 4 forming substance containing hydroxyl groups, and also containing'in solutiona Water soluble alkyloxy alkyl cellulose mixed ether containing ether'groups and also containing free hydroxyl groups formed by the reaction of an alkali cellulose with about-l mol of an alkylati'ng agent and about-3 mols of an, alkoxylating agent'calculatedper' eachrnol of glucose anhydride of saidj'alkalicellulose;

' and heating the thus treatedcellulose textile rnateri'al'to i said temperature so as toconvert said waterrsoluble resineforming substancedntoan insoluble resinous sub- ;stance and to causejcross linking reaction between the treated cellulose textile material to said predetermined temperature 'so as to convert saidwater soluble resinforming substance into an insoluble resinous substance.

and to cause cross linking reaction between the same and said water solublev alkylox-y alkyl cellulose, thereby form-' ing a treated cellulose textile material having improved properties; t

i 5. Method of improving properties such as the crease resistance and non-shrinkingproperties of cellulose textiles, comprising the steps of treatingacellulose textile material with an acid aqueous liquor containing in solu tion a Water soluble resin-forming substance which upon same' and saidwater soluble alkyloxy alkyl cellulose, thereby forming a treated'cellulose textile'rnaterial having improved properties.

"8. Method of improving properties such as the crease resistance and non-shrinking of celluloseitextiles, corn prising the steps of treating a .cellulose'textile material with an acid aqueousliqu'or havingla pH between 3 and 5 and containingr in solution a Water soluble resin-forming substancewhich upon heating to a predetermined temperature below the temperature at which damage to heatingto a predeterminedtemperature below the temperature at which damage tosaid cellulose textile ma--;; terial occurs is'transformed into an insoluble resinous substance,said water soluble resin-forrning substance containing'hydroxyl groups; and also containing in solution 1-5 g. fper'liter of a water soluble alkyloxy alkyl cellu- I lose mixed ethercontaining ether groups and also con taining'freehydroxyl groups formed by the reaction of 7 an alkali cellulose with about 1 mol. of an alkylating agent and about 3 mols of an alkoxylating agentcal-- culated per each mol of glucoseanhydride of said alkali cellulosejand heating the thus treated cellulose textile material to said predetermined temperature's'o as to convert said water soluble resin-forming substance into an said cellulose textile'material occurs, is transformed into an insoluble resinous substance, said water soluble resinforming substance containing 'hydroxyl groups, and also containing in solution a water soluble alkyloxy alkyl cellulose mixed ether containing ether groups'and also containing free hydroxyl groups formed by thereaction of an alkali cellulose with about 1 f mol, of an 'a lkylatingagent selected from the group consisting of methylbromide, methyl chloride ,.e'thyl bromide and ethyl chloride 2' and about 3 rnols of arralkoxylating agent-selectedfrom 40' the group consisting of ethylene oxide; propylene" oxide and ethylene: chlorohydrini;calculated per each mol .of

"glucose anhydride 'ofsaid alkali'cellulose; and heating the thus treated cellulose te'xtile 'rnaterial to saidlpredetermined temperature so as to convert saidf-Water soluble resin-forming substance; and aninsolubleresinous sub-I V stance and to cause: cross linkingr eaction between'the insoluble resinous substance and to cause cross linking reaction between the same and said Water' -soluble alkyloxy'ialkyl cellulose, thereby forming a treated cellulose textile-material having improved properties.

6.,Metho d of improving properties such as the crease resistance and 'nonshrinking properties of cellulose textiles,- comprising the steps of treating a cellulose textile material with an acid aqueous liquor containing in solu-- tion a 'waterisoluble resin-forming ,substancelwhiich upon heating to atemperature between 1.00 and 150 is transformed into an insoluble resinous substance; said '.water soluble resin-forming substance containing/hydroxyl groups, and "also containing in solution 1-;5 g.

' per liter of a Water soluble alkyloxy alkyl cellulose mixed ether containing ether groups and also containing;

same and saidfiwater soluble i alkyloxyfalkyl f'cellulos e, j thereby? forming a treated'cellulose textile material hav-v I ingirnprovedproperties; 1 W I 7 9; Method 'of improving properties such asthe'crease resistanceand' non-shrinking properties o f -cellulose texcontaining in solution 15 g; per:lite r;of a watersoluble.

tiles, comprising the stepsof treatingla cellulose textile "material with'an acid aqueous liquor' haying av pH'be tween 3 and, 5 and containing in solution a wate'r solublei resin-forming" substance which' upon heating'to atem perature between and 15Q-C,. is trahsforrned into an insoluble resinous substance,"said*watersoluble'resinforming substance. containingfhydroxylsgro lps; and also alkylo xy alkyl cellulosejmixed ether containingether groups'-andialso::containing :free hydroxyl groups formed free hydroxyl groupsforrried by the reaction'of anjalkali cellulose with about 1 mol of an alkylating agent selected from the group consisting of methyl bromide, methyl chloride, ethyl bromide and ethyl chloride and about 3 mols of an alkoxylating agent selectedfrom the groups consisting of ethylene oxide, propylene oxide and ethyl ene'jchlorohydrin calculated per each mol ofglucose'an- :hydride of said alkali cellulose; and vheating the thus treated'ccllulose textilermaterial to said temperature so as to convert said water soluble resin-forming substance 'inginiprovedproperties;'

by the reaction 1 of" an alkali I celluloselwith about "1 fmol "of an alkylating agent"selected from the group;consist ing of methyl bromide, methyl chloride, 'eth yl bromide andiethyl chloride and about 3 mols of ani,,alkoxylating. agent selected from thegroup consisting of ethylene oxide; propylene oxide-and ethylene. chlorohydrin calculated pereach' molof glucose 'anhydridef of said'. alkali cellulose; and heating the thus/treated cellulose textile material to saiditemperature so asto convert said water soluble resin-forming substance into an insoluble resinous substance andto} cause cross 'linking'reaction between the 7 same and" said water :solubleLalkyloxy alkyl cellulose,

thereby forming atreated cellulose textileirnaterialihavs 10. Method of improving properties such as the crease resistance and non-shrinking properties of cellulose textiles, comprising the steps of treating a cellulose textile material with an acid aqueous liquor containing in solution a water soluble resin-forming substance selected from the group consisting of formaldehyde, glyoxal, dimethylol urea, methylol urea, melamine-formaldehyde condensate, methylol biuret, dimethylol biuret and the reaction product of methylol urea and glyoxal which upon heating to a predetermined temperature below the temperature at which damage to said cellulose textile material occurs is transformed into an insoluble resinous substance, said water-soluble resin-forming substance containing hydroxyl groups, and also containing in solution a water soluble alkyloxy alkyl cellulose mixed ether containing ether groups and also containing free hydroxyl groups formed by the reaction of an alkali cellulose with about 1 mol of an alkylating agent and about 3 mols of an alkoxylating agent calculated per each mol of glucose anhydride of said alkali cellulose; and heating the thus treated cellulose textile material to said predetermined temperature so as to convert said water soluble resinforming substance into an insoluble resinous substance and to cause cross linking reaction between the same and said water soluble alkyloxy alkyl cellulose, thereby forming a treated cellulose textile material having improved properties.

11. Method of improving properties such as the crease resistance and non-shrinking properties of cellulose textiles, comprising the steps of treating a cellulose textile material with an acid aqueous liquor having a pH between 3 and 5 and containing in solution a Water soluble resin-forming substance selected from the group consisting of formaldehyde, glyoxal, dimethylol urea, methylol urea, melamine-formaldehyde condensate, methylol biuret, dimethylol biuret and the reaction product of methyiol urea and glyoxal which upon heating to a termperature between and C. is transformed into an insoluble resinous substance, said water soluble resinforming substance containing hydroxyl groups, and also containing in solution a water soluble alkyloxy alkyl cellulose containing ether groups and also containing free hydroxyl groups formed by the reaction of an alkali alkyl cellulose mixed ether With about 1 mol of an alkylating agent and about 3 mols of an alkoxylating agent calculated per each mol of glucose anhydride of said alkali cellulose; and heating the thus treated cellulose textile material to said temperature so as to convert said water soluble resin-forming substance into an insoluble resinous substance and to cause cross linking reaction between the same and said water soluble alkyloxy alkyl cellulose, thereby forming a treated cellulose textile materialhaving improved properties.

References Cited in the file of this patent UNITED STATES PATENTS 1,505,043 Lilienfeld Aug. 12, 1924 2,190,451 Haskins Feb. 13, 1940 2,469,431 Broderick May 10, 1949 2,644,818 Downing et a1. July 7, 1953 2,672,427 Bauling et a1 Mar. 16, 1954 2,949,452 Savage Aug. 16, 1960 

1. METHOD OF IMPROVING PROPERTIES SUCH AS THE CREASE RESISTANCE AND NON-SHRINKING PROPERTIES OF CELLULOSE TEXTILES, COMPRISING THE STEPS OF TREATING A CELLULOSE TEXTILE MATERIAL WITH AN ACID AQUEOUS LIQUOR CONTAINING IN SOLUTION A WATER SOLUBLE RESIN-FORMING SUBSTANCE WHICH UPON HEATING TO A PREDETERMINED TEMPRATURE BELOW THE TEMPERATURE AT WHICH DAMAGE TO SAID CELLULOSE TEXTILE MATERIAL OCCURS IS TRANSFORMED INTO AN INSOLUBLE RESINOUS SUBSTANCE, SAID WATER SOLUBLE RESIN-FORMING SUBSTANCE CONTAINING HYDROXYL GROUPS, AND ALSO CONTAINING IN SOLUTION A WATER SOLUBLE ALKYLOXY ALKYL CELLULOSE MIXED ETHER CONTAINING ETHER GROUPS AND ALSO CONTAINING FREE HYDROXYL GROUPS FORMED BY THE REACTION OF AN ALKALI CELLULOSE WITH ABOUT 1 MOL OF AN ALKYLATING AGENT AND ABOUT 3 MOLS OF AN ALKOXYLATING AGENT CALCULATED PER EACH MOL OF GLUCOSE ANHYDRIDE OF SAID ALKALI CELLULOSE; AND HEATING THE THUS TREATED CELLULOSE TEXTILE MATERIAL TO SAID PREDETERMINED TEMPERATURE SO AS TO CONVERT SAID WATER SOLUBLE RESIN-FORMING SUBSTANCE INTO AN INSOLUBLE RESINOUS SUBSTANCE AND TO CAUSE CROSS LINKING REACTION BETWEEN THE SAME AND SAID WATER SOLUBLE ALKYLOXY ALKYL CELLULOSE, THEREBY FORMING A TREATED CELULOSE TEXTILE MATERIAL HAVING IMPROVED PROPERTIES. 